Regio- and stereochemical aspects in the synthesis of homoallylic alcohols from benzoins and their iodocyclisation to 2,3-diphenyltetrahydrofurans

Tetrahedron

Volumn 62, Issue 17, 2006, Pages 4018-4026

  Kumar, Subodh ^a   Kaur, Pervinder ^a   Mittal, Anu ^a   Singh, Palwinder ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Benzoins; Diphenyltetrahydrofurans; Homoallylic alcohols; Indium; Iodocyclisation; Regioselective

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; BENZOIN; INDIUM; ORGANOMETALLIC COMPOUND; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33645971287     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.031     Document Type: Article

References (41)

1. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293
2. Miller S.J., Blackwell H.E., and Grubbs R.H. J. Am. Chem. Soc. 118 (1996) 9606-9614
3. Felpin F.X., Girard S., Vo-Thanh G., Robins R.J., Villieras J., and Lebreton J. J. Org. Chem. 66 (2001) 6305-6312
4. Loh T.P., Hu Q.Y., and Ma L.T. J. Am. Chem. Soc. 123 (2001) 2450-2451
5. Adam W., Saha-Moller C.R., and Schmid K.S. J. Org. Chem. 66 (2001) 7365-7371
6. For reviews see: (a). Cintas P. Synlett (1995) 1087-1096
7. Li C.J. Tetrahedron 52 (1996) 5643-5668
8. Li C.J., and Chan T.H. Tetrahedron 55 (1999) 11149-11176
9. Ranu B.C. Eur. J. Org. Chem. 13 (2000) 2347-2356
10. Podlech J., and Maier T.C. Synthesis (2003) 633-655
11. Nair V., Ros S., Jayan C.N., and Pallai B.S. Tetrahedron 60 (2004) 1959-1982
12. Chauhan K.K., and Frost C.G. J. Chem. Soc., Perkin Trans. 1 (2000) 3015-3019
13. Fringuelli F., Piermatti O., Pizzo F., and Vaccaro L. Curr. Org. Chem. 7 (2003) 1661-1689
14. Kumar S., Kaur P., and Kumar V. Curr. Org. Chem. 9 (2005) 1205-1235
15. Li C.J., and Chan T.H. Organic Reactions in Aqueous Media (1997), Wiley, New York
16. Li C. J. Chem. Rev. 93 (1993) 2023-2035
17. Lubineau A., Auge J., and Queneau Y. In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Blackie, Glasgow
18. Paquette L.A., and Lobben P.C. J. Am. Chem. Soc. 118 (1996) 1917-1930
19. Li C.J., and Zhang W.C. J. Am. Chem. Soc. 120 (1998) 9102-9103
20. Wada M., Fukuma T., Morioka M., Takahashi T., and Miyoshi N. Tetrahedron Lett. 38 (1997) 8045-8048
21. Pirrung M.C., and Sarma K.D. J. Am. Chem. Soc. 126 (2004) 444-445
22. Kumar S., and Kaur P. Tetrahedron Lett. 45 (2004) 3413-3416
23. Paquette L.A., and Mitzel T.M. J. Am. Chem. Soc. 118 (1996) 1931-1937
24. Paquette L.A., and Mitzel T.M. Tetrahedron Lett. 36 (1995) 6863-6866
25. Paquette L.A., Bennett G.D., Isaac M.B., and Chhatriwala A. J. Org. Chem. 63 (1998) 1836-1845
26. Paquette L.A., and Mitzel T.M. J. Org. Chem. 61 (1996) 8799-8804
27. Paquette L.A., Mitzel T.M., Isaac M.B., Crasto C.F., and Schomer W.W. J. Org. Chem. 62 (1997) 4293-4301
28. Paquette L.A., and Lobben P.C. J. Org. Chem. 63 (1998) 5604-5616
29. Lobben P.C., and Paquette L.A. J. Org. Chem. 63 (1998) 6990-6998
30. Paquette L.A., and Lobben P.C. J. Am. Chem. Soc. 118 (1996) 1917-1930
31. Loh T., Ho D.S., Chua G., and Sim K. Synlett (1997) 563-564
32. Carda M., Castillo E., Rodriguez S., Murga J., and Marco J.A. Tetrahedron: Asymmetry 9 (1998) 1117-1120
33. Preliminary communication. Kumar S., Kaur P., Singh P., and Chimnni S.S. Synlett (2001) 1431-1433
34. Garg R., Kurup A., Mekapati S.B., and Hansch C. Chem. Rev. 103 (2003) 703-731
35. Prasit P., Wang Z., Brideau C., Chan C.C., Charleson S., Cromlish W., Ethier D., Evans J.F., Ford-Hutchinson A.W., Gauthier J.Y., Gordon R., Guay J., Gresser M., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neill G.P., Ouellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Therien M., Vickers P., Wong E., Xu L.-J., Young R.N., Zamboni R., Boyce S., Rupniak N., Forrest M., Visco D., and Patrick D. Bioorg. Med. Chem. Lett. 9 (1999) 1773-1778
36. Talley J.J., Brown D.L., Carter J.S., Graneto M.J., Koboldt C.M., Masferrer J.L., Perkins W.E., Rogers R.S., Shaffer A.F., Zhang Y.Y., Zweifel B.S., and Seibert K. J. Med. Chem. 43 (2000) 775-777
37. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., and Isakson P.C. J. Med. Chem. 40 (1997) 1347-1365
38. Yasuda M., Fujibayashi T., and Baba A. J. Org. Chem. 63 (1998) 6401-6404
39. Paquette L.A., and Rothhaar R.R. J. Org. Chem. 64 (1999) 217-224
40. Kaur P., Singh P., and Kumar S. Tetrahedron 61 (2005) 8231-8234
41. Labelle M., Morton H.E., Guindon Y., and Springer J.P. J. Am. Chem. Soc. 110 (1998) 4533-4540